Fast, Facile and Convenient Synthesis
53
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1605, 1555, 1427, 1302, 1265, 1141, 782 cm−1; H NMR (400 MHz, CDCl3): δ 7.61
(2H, sbr, 2CH=), 7.20-7.37 (6H, Ar), 2.47 (4H, m, 2CH2), 1.74 (2H, m, CH2); 13C NMR
(100 MHz, CDCl3): δ= 21.97, 28.24, 127.98, 129.48, 132.29, 134.17, 134.45, 140.16,
188.04; Anal. Calcd for C20H14 Cl4O: C, 58.29; H, 3.42; Found: C, 59.08; H, 3.63.
Entry 24: IR (KBr): 3045, 2936, 2915, 1679, 1621, 1568, 1444, 1307, 1265, 913, 782
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cm−1; H NMR (400 MHz, CDCl3): δ 7.60 (2H, sbr, 2CH=), 7.03-7-39 (6H, Ar), 2.54
(4H, m, 2CH2), 1.73 (2H, m, CH2); 13C NMR (100 MHz, CDCl3): δ= 22.41, 28.70,
28.75, 114.16, 114.39, 123.34, 123.53, 125.30, 125.33, 128.21, 130.03, 130.12, 135.29,
135.34, 140.69, 158.51, 161.01, 188.24; Anal. Calcd for C20H14Cl2F2O: C, 63.34; H,
3.72; Found: C, 63.56; H, 3.38. Entry 34: IR (KBr): 3065, 2955, 2926, 1673, 1613,
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1468, 1435, 1298, 1238, 1145, 1051, 755 cm−1; H NMR (400 MHz, CDCl3): δ 7.95
(2H, sbr, 2CH=), 7.29-7.46 (8H, Ar), 2.86 (2H, m, 2H of CH2), 2.42 (2H, m, 2H of
CH2), 1.89 (1H, m, CH), 1.02 (3H, d, J = 6.4 Hz, Me); 13C NMR (100 MHz, CDCl3): δ=
21.50, 29.64, 36.42, 126.38, 129.69, 129.77, 130.62, 134.35, 135.06, 136.90, 189.45;
Anal. Calcd for C21H18 Cl2O: C, 70.60; H, 5.08; Found: C, 71.10; H, 5.73. Entry 37: IR
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(KBr): 3065, 2956, 2926, 1679, 1621, 1567, 1445, 1299, 1246, 1143, 911, 782 cm−1; H
NMR (400 MHz, CDCl3): δ 7.61 (2H, sbr, CH=), 7.25-7.32 (4H, Ar), 7.04-7.08 (2H,
Ar), 2.55 (2H, m, 2H of CH2), 2.30 (2H, m, 2H of CH2), 1.91 (1H, m, CH), 0.97 (3H, d,
J= 6.4 Hz, Me); 13C NMR (100 MHz, CDCl3): δ= 21.24, 28.76, 36.63, 36.68, 114.20,
114.43, 123.34, 123.53, 125.31, 125.35, 128.52, 130.05, 130.15, 135.29, 135.33,
139.85, 158.50, 161.00, 188.02; Anal. Calcd for C21H16Cl2F2O: C, 64.14; H, 4.10;
Found: C, 64.03; H, 4.25. Entry 38: IR (KBr): 3085, 2925, 2884, 1672, 1611, 1528,
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1349, 1299, 1196, 1147 cm−1; H NMR (400 MHz, CDCl3): δ 8.29 (2H, sbr, 2CH=),
8.20-8.22 (2H, Ar), 7.61-7.81 (6H, Ar), 3.05 (2H, dd, J = 3.6, 16.0 Hz, 2H of 2CH2),
2.62 (2H, ddd, J = 2.4, 12.0, 16.0 Hz, 2H of 2CH2), 1.98 (1H, m, CH), 1.12 (3H, d, J =
6.8 Hz, Me); 13C NMR (100 MHz, CDCl3): δ= 21.45, 29.10, 36.08, 123.29, 124.55,
129.57, 134.90, 136.08, 137.20, 137.29, 148.25, 188.95; Anal. Calcd for C21H18 N2O5:
C, 66.66; H, 4.79; Found: C, 67.13; H, 4.54. Entry 39: IR (KBr): 3031, 2927, 2879,
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1655, 1609, 1582, 1295, 1212, 1148, 971 cm−1; H NMR (400 MHz, CDCl3): δ 6.98-
8.55 (16H, Ar & 6CH=), 3.02 (2H, dd, J = 3.2, 15.8 Hz, 2H of 2CH2), 2.35 (2H, m, 2H
of CH2), 2.01 (1H, m, CH), 1.21 (3H, d, J = 6.4 Hz, Me); 13C NMR (100 MHz, CDCl3):
δ= 21.75, 28.45, 34.79, 123.71, 127.24, 128.84, 128.90, 134.70, 136.56, 136.77, 140.83,
188.74; Anal. Calcd for C25H24O: C, 88.20; H, 7.11; Found: C, 87.89; H, 7.04. Entry
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40: IR (KBr): 3054, 2953, 2923, 1665, 1605, 1503, 1296, 1227, 1145, 1004 cm−1; H
NMR (400 MHz, CDCl3): δ 8.09 (2H, sbr, CH=), 7.54-8.04 (14H, Ar), 3.22 (2H, dd, J
= 3.6, 15.8 Hz, 2H of CH2), 2.68 (2H, ddd, J = 2.4, 11.4, 15.2 Hz, 2H of CH2), 1.98 (1H,
m, CH), 1.13 (3H, d, J = 6.8 Hz, Me); 13C NMR (100 MHz, CDCl3): δ= 21.69, 29.52,
36.66, 126.49, 126.92, 127.70, 127.72, 127.86, 127.99, 128.50, 130.32, 133.11, 133.14,
133.59, 135.69, 137.36, 190.08; Anal. Calcd for C29H24O: C, 89.66; H, 6.23; Found: C,
90.11; H, 6.36.
Conclusion
In conclusion, we have developed a easy, effective, quick and cost-effective procedure for
the synthesis of α,α-bis(substituted-arylidene) cycloalkanones using commercially available
KOH under mild conditions. Moreover, the high yield of products, no work-up need, ready
availability of the catalyst, compatibility with various functional groups and the clean
procedure, will make the present method a useful and important addition to the present
methodologies for this synthesis.